Sodium borohydride → Ethyl 2-(3-(2-(3-(2-quinolinylmethyloxy)phenyl)-2-hydroxyethyl)phenoxy)acetate

HRID 2073907Notes

Reaction equation

HRID 2073907 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:14]=[C:15]([C:19](=[O:34])[CH2:20][C:21]2[CH:22]=[C:23]([CH:31]=[CH:32][CH:33]=2)[O:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:16]=[CH:17][CH:18]=1.[BH4-].[Na+]>CCO.O>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:14]=[C:15]([CH:19]([OH:34])[CH2:20][C:21]2[CH:22]=[C:23]([CH:31]=[CH:32][CH:33]=2)[O:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 14774137Ethyl 2-(3-(2-(3-(2-quinolinylmethyloxy)phenyl)-2-oxoethyl)phenoxy)acetate

Product 1

HCID 14774138Ethyl 2-(3-(2-(3-(2-quinolinylmethyloxy)phenyl)-2-hydroxyethyl)phenoxy)acetate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

The product obtained from Step B (5 mmol) in 50 mL of EtOH is treated with (2 mmol) of NaBH4 at room temperature. After 30 min, the reaction mixture is diluted with water and extracted with EtOAc. The organic solution is dried and evaporated and purified by dry column chromatography to give ethyl 2-(3-(2-(3-(2-quinolinylmethyloxy)phenyl)-2-hydroxyethyl)phenoxy)acetate.

Workup

  1. extractionextracted with EtOAc
  2. customThe organic solution is dried
  3. customevaporated
  4. custompurified
  5. customby dry column chromatography

Sources & evidence

ORD record
ord-8300174cf1b942c1856094dc8b999309
Source dataset
uspto-grants-1990_04
Patent number
US04920131

Reaction notes

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